Their first time
by BiebSwaggy
Summary: What would happen if Darren Criss and Tyler Oakley would be a couple and how would their first time be when Tyler is the first boyfriend Darren ever had? Virgin!Darren


Dating Tyler brought new worries to Darren's life. One of them was the sex.

Maybe he wasn't the unknown kid anymore but it didn't mean he was a sex god either. Tyler was the first boy he ever dated and he never went all the way with a girl. And if Tyler would be a virgin too, it would be fine but he wasn't and that scared him.

First, Tyler was gay since years. Which, obviously, meant he must have been more experienced. And Darren was sure it could mean only one thing – a handjob or a blowjob here and there wouldn't satisfy the him. That's why one evening, not long after they had started dating, Darren found himself in Tyler's bed, pulling out a condom with a shaky hand and placing it into his boyfriend's hand. The other boy stopped kissing him instantly and faced him.

"What is this?" he asked.

"Um, a condom, I guess," Darren smiled uncomfortably from where he was lying on the bed.

Tyler lifted himself from the boy. "Don't you think it's a bit too soon for us to have sex?" he asked caressing Darren's cheek with his thumb and smiling softly.

"I don't know… I was just thinking that you may want–"

"Stop right here. It's not about what I want. It's about what _we_ _both_ want. I can see you are not ready and personally I think we should wait a bit longer."

Darren watched him with a slight hurt on his face that, he hoped, was hidden from his boyfriend but, unfortunately for him, Tyler could see right through him.

"Hey, don't look like that," he smiled and gave him a chaste kiss on his lips. "It's not that I don't want you. Believe me. I just don't want you to feel pushed or anything. I will never push you to do anything you are not ready to do. Okay?"

Darren gave him a thankful smile and kissed him. "Thanks."

"Now, can we please kiss some more? I already miss your lips."

* * *

The next almost four months the couple went on dates, watched movies together and were just cute. They also spent nights in each other's arms every so often and cuddled till they fell asleep in each others arms.

"So, would you like to come over this weekend" Darren found himself asking one day when they were leaving Taco Bell

"Do I ever _not_ want to spend time with you and come over?" Tyler asked smiling

"Good question," Darren smiled. "I was thinking. I think, I'm ready."

"Ready?" Tyler questioned.

"Yes, ready. For sex, I mean."

''You think you are ready?'' Tyler asked

''Yeah, I mean I am I was just thinking if it's still too soon for you." Darren said.

Tyler took his hand and squeezed it gently. "Are you sure? It's a big step. I want you to be confident about your choice."

"I am. I really want to do it with you. I want you to be my first."

"Thank you," he smiled affectionately. "Just know that if you change your mind at any moment, all you need to do is tell me."

''So you come over?''

''Yeah.''

* * *

Whenever Darren had thought about his first time, he was scared. But now that he had finally made up his mind, he was just very exited.

He changed the sheets, placed a bottle of lube and a condom on the nightstand, and waited impatiently for his boyfriend to come, while preparing the dinner.

It was almost eight when he heard someone knocking on the door and he went quickly to open it, to find Tyler with a single red rose standing before him.

"Good evening, honey," he said and leaned for a kiss.

"Evening," Darren said and kissed the man, who extended the flower to him. "Thank you. You didn't need to"

"But I wanted to" Tyler said. "Is it chicken I smell?"

Darren nodded and let his boyfriend walk into the his house, shutting the door after him.

Tyler settled by the table, eating dinner normally as if it was just another evening together but they could both feel the anticipation in the air.

"Do you want some ice-cream for a dessert now?" Darren asked being a polite host, who just happened to know about Tyler's sweet tooth.

"I want something else for the dessert," he answered and captured Darren's lips with his.

Not long after they were both on the bed panting into a heated kiss, clothes being removed one by one.

"You are so hot," Tyler said kissing Darren's now naked body. "I want you so bad."

"Me too," Darren answered and all coherent thoughts left his mind as Tyler lowered his head and wrapped his lips around Darren's hardening cock.

So far from what they had been doing, this was his favourite activity. Seeing his boyfriend bobbing his head up and down, lips stretched around him, was the sexiest sight in the world as well as the best feeling ever.

Unfortunately, it didn't take long because Tyler had different plans for him and Darren coming into his throat wasn't one of them. So he released Darren's cock from his mouth and crawled up to kiss him hungrily while thrusting his dry cock against Darren's slick one.

"Want… you," Darren managed through his moans. "Please."

Tyler smiled against his lips and sat up, reaching for lube and the condom.

"Spread your legs for me, gorgeous," he instructed and lubed up his fingers.

Fingering wasn't new for them; they had done it many times before but Darren knew it would be different now because it wasn't about him coming from his boyfriend's fingers; it was about preparation for more.

Once the lube was relatively warm, Tyler brought his hand to Darren's entrance and teased his rim with one finger for a moment. Usually he enjoyed teasing but this night he wanted to focus on one thing only – making Darren's first experience as enjoyable as possible.

Very slowly he pushed one index finger inside Darren and let him adjust to the stretch. Soon the second finger joined, and then the third.

"I'm… ready," Darren panted. "Please, now… or I will… come."

Tyler removed his fingers slowly. "Are you still sure about this?" he asked putting a condom on and pouring a generous amount of lube over his cock.

"Yes, I'm sure."

"Okay," he said and lowered himself on his boyfriend again. "Thank you for trusting me and letting me be your first."

"I love you," Darren said looking straight into Tyler's eyes.

"I love you too," Tyler smiled and gently kissed the boy while slowly pushing in.

It was nothing like what Darren had experienced before. Fingers were nice but being this full was totally different. And it hurt much more.

"Are you okay, beautiful?" Tyker asked when he finally stilled inside his boyfriend.

"Yeah," Darren breathed trying his best to relax his muscles in hopes for the pain to go away. "Aren't you supposed to move?"

Tyler giggled. "No, I'm supposed to give you a few minutes to get used to me being inside you. Only then I'm supposed to move. Though I must say, you are so tight that I'm having difficulties here."

Darren frowned. "I'm sorry, I–"

"Darren, sweetie, that's a good thing," he said. "It just feels so good that I can hardly stop myself from mercilessly slamming into you."

"It really feels good for you?"

"It does. And I promise it will feel good for you as well once the pain subsides. I will make sure you have the best orgasm ever."

The conversation helped. It took Darren's mind off things and he felt his muscles relax. They spent a few more minutes just lazily kissing until Darren could feel only remainder of pain.

"You can move if you want," he said breaking the kiss.

Tyler didn't say anything, just carefully raised himself on his elbows and slowly pulled out and pushed in again.

"Oh, shit," Darren moaned.

"Okay?" Tyler asked moving inside him.

"More than okay," Darren said and minutes later added, "You can go faster." And Tyler was more than happy to comply. Soon they were both sweaty and incoherent.

"Close," Darren said through his moans and Tyler, who felt like he would come any second, grabbed Darren's cock in his hand and started pumping it at the same pace as his thrusts'.

"Fuck!" Darren screamed as he came all over his stomach and Tyler's hand.

His boyfriend soon followed and after coming back from his high, he pulled out of Darren. After discarding the condom and cleaning both of them he lay down next to the boy he loved and kissed him.

"How are you feeling?" Tyler asked looking at Darren's blissful face.

"Happy," Darren answered and snuggled at his side.


End file.
